Just curious, what about scp-ing to your server is less than ideal for you? I would think a static server with nginx or similar would be an easy one time setup and then you do a single command to scp to it whenever you want to add images. No redeploy necessary. I would almost consider that easier than other bespoke solutions that you would have to learn

I can’t compare to fastmail since I haven’t used it, but I’ve been very happy with proton mail.

I’m definitely in the “for almost everything” camp. It’s less ambiguous especially when you consider the DD/MM vs MM/DD nonsense between US dates vs elsewhere. Pretty much the only time I don’t use ISO-8601 is when I’m using non-numeric month names like when saying a date out loud.